JP3113237B2 - チアゾール誘導体 - Google Patents
チアゾール誘導体Info
- Publication number
- JP3113237B2 JP3113237B2 JP11000010A JP1099A JP3113237B2 JP 3113237 B2 JP3113237 B2 JP 3113237B2 JP 11000010 A JP11000010 A JP 11000010A JP 1099 A JP1099 A JP 1099A JP 3113237 B2 JP3113237 B2 JP 3113237B2
- Authority
- JP
- Japan
- Prior art keywords
- amino
- thiazole
- acid
- carbonyl
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000007979 thiazole derivatives Chemical class 0.000 title description 4
- -1 3-benzyl-ureido Chemical group 0.000 claims description 260
- 150000001875 compounds Chemical class 0.000 claims description 206
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 86
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 150000002148 esters Chemical class 0.000 claims description 45
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 19
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- 206010028980 Neoplasm Diseases 0.000 claims description 18
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- 108010048673 Vitronectin Receptors Proteins 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
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- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 12
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- 102000004169 proteins and genes Human genes 0.000 claims description 12
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- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 9
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- 125000003277 amino group Chemical group 0.000 claims description 9
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
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- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 claims description 8
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 8
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- 239000000126 substance Substances 0.000 claims description 8
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 230000001771 impaired effect Effects 0.000 claims description 6
- 229960003136 leucine Drugs 0.000 claims description 6
- JKPFGHHEGIRDMB-UHFFFAOYSA-N 5-[3-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]anilino]-5-oxo-3-pyridin-3-ylpentanoic acid Chemical compound N1=C(NC(N)=N)SC(C=2C=C(NC(=O)CC(CC(O)=O)C=3C=NC=CC=3)C=CC=2)=C1C JKPFGHHEGIRDMB-UHFFFAOYSA-N 0.000 claims description 5
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 5
- 239000004395 L-leucine Substances 0.000 claims description 5
- 235000019454 L-leucine Nutrition 0.000 claims description 5
- 229930182821 L-proline Natural products 0.000 claims description 5
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 5
- 230000009401 metastasis Effects 0.000 claims description 5
- 125000005936 piperidyl group Chemical group 0.000 claims description 5
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- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 5
- ORQXBVXKBGUSBA-QMMMGPOBSA-N β-cyclohexyl-alanine Chemical compound OC(=O)[C@@H](N)CC1CCCCC1 ORQXBVXKBGUSBA-QMMMGPOBSA-N 0.000 claims description 5
- HEPOIJKOXBKKNJ-UHFFFAOYSA-N 2-(propan-2-ylazaniumyl)acetate Chemical compound CC(C)NCC(O)=O HEPOIJKOXBKKNJ-UHFFFAOYSA-N 0.000 claims description 4
- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 claims description 4
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 4
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- 239000004473 Threonine Substances 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 4
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- OFYAYGJCPXRNBL-LBPRGKRZSA-N naphthalen-2-yl-3-alanine Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CC=CC2=C1 OFYAYGJCPXRNBL-LBPRGKRZSA-N 0.000 claims description 4
- 229960001153 serine Drugs 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 229960002898 threonine Drugs 0.000 claims description 4
- JPZXHKDZASGCLU-LBPRGKRZSA-N β-(2-naphthyl)-alanine Chemical compound C1=CC=CC2=CC(C[C@H](N)C(O)=O)=CC=C21 JPZXHKDZASGCLU-LBPRGKRZSA-N 0.000 claims description 4
- AKZXPYXTNXTEIN-NSHDSACASA-N (2s)-2-[[2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 AKZXPYXTNXTEIN-NSHDSACASA-N 0.000 claims description 3
- XEUFLBBKEOMEIN-UHFFFAOYSA-N 6-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]-5-oxohexanoic acid Chemical compound OC(=O)CCCC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 XEUFLBBKEOMEIN-UHFFFAOYSA-N 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 3
- SEKDTNQJEXCBDK-RSAXXLAASA-N (3s)-3-[[2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-4-(2-methylpropylamino)-4-oxobutanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC(C)CNC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 SEKDTNQJEXCBDK-RSAXXLAASA-N 0.000 claims description 2
- CNAZETNVGHCEEP-FERBBOLQSA-N (3s)-4-(benzylamino)-3-[[2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-4-oxobutanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N([C@@H](CC(=O)O)C(=O)NCC=1C=CC=CC=1)C(=O)CNC(=O)C(N=1)=CSC=1NC(=O)NCC1=CC=CC=C1 CNAZETNVGHCEEP-FERBBOLQSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 166
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 134
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
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- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- YRTOIWNETUADLY-UHFFFAOYSA-N chlorosulfonyl nitrate Chemical compound [O-][N+](=O)OS(Cl)(=O)=O YRTOIWNETUADLY-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- NNTWHUAEOGQHFD-UHFFFAOYSA-N diethyl 2-(3-amino-2-oxopropyl)butanedioate Chemical compound CCOC(=O)CC(CC(=O)CN)C(=O)OCC NNTWHUAEOGQHFD-UHFFFAOYSA-N 0.000 description 1
- DSPQPSYCMIMDRI-UHFFFAOYSA-N diethyl 2-(3-azido-2-oxopropyl)butanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)CC(=O)CN=[N+]=[N-] DSPQPSYCMIMDRI-UHFFFAOYSA-N 0.000 description 1
- KDYGRRJEHAZMTH-UHFFFAOYSA-N diethyl 2-(3-bromo-2-oxopropyl)butanedioate Chemical compound CCOC(=O)CC(CC(=O)CBr)C(=O)OCC KDYGRRJEHAZMTH-UHFFFAOYSA-N 0.000 description 1
- XNFJIAUTENROSE-UHFFFAOYSA-N diethyl 2-[3-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]-2-oxopropyl]butanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)CC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 XNFJIAUTENROSE-UHFFFAOYSA-N 0.000 description 1
- VKUFRHGDKCVHCE-UHFFFAOYSA-N diethyl 3-[4-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]phenyl]pentanedioate Chemical compound C1=CC(C(CC(=O)OCC)CC(=O)OCC)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 VKUFRHGDKCVHCE-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- XCJPURWRBADMGT-KRWDZBQOSA-N ditert-butyl (2s)-2-[[2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]butanedioate Chemical compound CC(C)(C)OC(=O)C[C@@H](C(=O)OC(C)(C)C)NC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 XCJPURWRBADMGT-KRWDZBQOSA-N 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- RZQDWFWACMUXFR-UHFFFAOYSA-N ethyl 2-(benzylcarbamoylamino)-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 RZQDWFWACMUXFR-UHFFFAOYSA-N 0.000 description 1
- LBSBQVAGEVSBQP-UHFFFAOYSA-N ethyl 2-(diaminomethylideneamino)-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(N=C(N)N)=N1 LBSBQVAGEVSBQP-UHFFFAOYSA-N 0.000 description 1
- LIBLLNBLKAGOQW-UHFFFAOYSA-N ethyl 2-(diaminomethylideneamino)-1,3-thiazole-4-carboxylate;hydrobromide Chemical compound Br.CCOC(=O)C1=CSC(NC(N)=N)=N1 LIBLLNBLKAGOQW-UHFFFAOYSA-N 0.000 description 1
- IIZWYNDWOXSKNC-UHFFFAOYSA-N ethyl 2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C=1SC(NC(N)=N)=NC=1C IIZWYNDWOXSKNC-UHFFFAOYSA-N 0.000 description 1
- JJMPHQKGNFNAEJ-UHFFFAOYSA-N ethyl 2-(pyridin-2-ylmethylcarbamoylamino)-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(NC(=O)NCC=2N=CC=CC=2)=N1 JJMPHQKGNFNAEJ-UHFFFAOYSA-N 0.000 description 1
- RAZNNERIXCQWAK-UHFFFAOYSA-N ethyl 2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 RAZNNERIXCQWAK-UHFFFAOYSA-N 0.000 description 1
- QSOBILXJDUDYOI-UHFFFAOYSA-N ethyl 2-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CSC(NC(N)=N)=N1 QSOBILXJDUDYOI-UHFFFAOYSA-N 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- PTABRRLBRPELAW-UHFFFAOYSA-N ethyl 3-(4-aminophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound CCOC(=O)CC(NC(=O)OC(C)(C)C)C1=CC=C(N)C=C1 PTABRRLBRPELAW-UHFFFAOYSA-N 0.000 description 1
- NEXFMPAUGJAIHE-UHFFFAOYSA-N ethyl 3-(4-aminophenyl)propanoate Chemical compound CCOC(=O)CCC1=CC=C(N)C=C1 NEXFMPAUGJAIHE-UHFFFAOYSA-N 0.000 description 1
- JONMELHQSPJECG-UHFFFAOYSA-N ethyl 3-(benzylcarbamoyl)-6-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]hexanoate Chemical compound C=1C=CC=CC=1CNC(=O)C(CC(=O)OCC)CCCNC(=O)C(N=1)=CSC=1NC(=O)NCC1=CC=CC=C1 JONMELHQSPJECG-UHFFFAOYSA-N 0.000 description 1
- JWKFIFMIXKNQAS-UHFFFAOYSA-N ethyl 3-[(2-aminoacetyl)amino]-3-pyridin-3-ylpropanoate Chemical compound CCOC(=O)CC(NC(=O)CN)C1=CC=CN=C1 JWKFIFMIXKNQAS-UHFFFAOYSA-N 0.000 description 1
- VQVSVDPSZLALAR-UHFFFAOYSA-N ethyl 3-[(3-amino-4-methoxybenzoyl)amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C1=CC=C(OC)C(N)=C1 VQVSVDPSZLALAR-UHFFFAOYSA-N 0.000 description 1
- DSNJPOAURPCUNU-UHFFFAOYSA-N ethyl 3-[(3-amino-5-phenylmethoxybenzoyl)amino]-3-phenylpropanoate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C(C=1)=CC(N)=CC=1OCC1=CC=CC=C1 DSNJPOAURPCUNU-UHFFFAOYSA-N 0.000 description 1
- AUVANWMAELELBU-UHFFFAOYSA-N ethyl 3-[3-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]propanoylamino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CCNC(=O)C1=CSC(NC(N)=N)=N1 AUVANWMAELELBU-UHFFFAOYSA-N 0.000 description 1
- JUWWGUMUVCLNGE-UHFFFAOYSA-N ethyl 3-[3-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]propanoylamino]propanoate Chemical compound CCOC(=O)CCNC(=O)CCNC(=O)C1=CSC(NC(N)=N)=N1 JUWWGUMUVCLNGE-UHFFFAOYSA-N 0.000 description 1
- VJOCSWOFCWONAL-UHFFFAOYSA-N ethyl 3-[3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]propanoylamino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CCNC(=O)C=1SC(NC(N)=N)=NC=1C VJOCSWOFCWONAL-UHFFFAOYSA-N 0.000 description 1
- WUQOWMVMOZXSFC-UHFFFAOYSA-N ethyl 3-[3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]propanoylamino]propanoate Chemical compound CCOC(=O)CCNC(=O)CCNC(=O)C=1SC(NC(N)=N)=NC=1C WUQOWMVMOZXSFC-UHFFFAOYSA-N 0.000 description 1
- IZCVFLFCTYRCKU-UHFFFAOYSA-N ethyl 3-[4-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]phenyl]-3-(butylsulfonylamino)propanoate Chemical compound C1=CC(C(CC(=O)OCC)NS(=O)(=O)CCCC)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 IZCVFLFCTYRCKU-UHFFFAOYSA-N 0.000 description 1
- RWEAHKOVFIYHMM-UHFFFAOYSA-N ethyl 3-[4-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]phenyl]-3-(propanoylamino)propanoate Chemical compound C1=CC(C(NC(=O)CC)CC(=O)OCC)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 RWEAHKOVFIYHMM-UHFFFAOYSA-N 0.000 description 1
- VSTKLGKQQSVKBV-UHFFFAOYSA-N ethyl 3-[4-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OCC)=CC=C1NC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 VSTKLGKQQSVKBV-UHFFFAOYSA-N 0.000 description 1
- QHVZNZCYLWDJNQ-UHFFFAOYSA-N ethyl 3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]benzoate Chemical compound CCOC(=O)C1=CC=CC(NC(=O)C2=C(N=C(NC(N)=N)S2)C)=C1 QHVZNZCYLWDJNQ-UHFFFAOYSA-N 0.000 description 1
- VWLHAXXQRUHAGI-UHFFFAOYSA-N ethyl 3-[[2-[[2-(4,5-dihydro-1h-imidazol-2-ylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-pyridin-3-ylpropanoate Chemical compound C=1C=CN=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C(N=1)=CSC=1N=C1NCCN1 VWLHAXXQRUHAGI-UHFFFAOYSA-N 0.000 description 1
- SEBKZAJINKUAOT-UHFFFAOYSA-N ethyl 3-[[2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-pyridin-3-ylpropanoate Chemical compound C=1C=CN=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C(N=1)=CSC=1NC(=O)NCC1=CC=CC=C1 SEBKZAJINKUAOT-UHFFFAOYSA-N 0.000 description 1
- ZZNPSQNHIMITTK-UHFFFAOYSA-N ethyl 3-[[2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]propanoate Chemical compound CCOC(=O)CCNC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 ZZNPSQNHIMITTK-UHFFFAOYSA-N 0.000 description 1
- UNTGBSIBMLUOJT-UHFFFAOYSA-N ethyl 3-[[2-[[2-(benzylcarbamoylamino)-5-methyl-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C(=C(S1)C)N=C1NC(=O)NCC1=CC=CC=C1 UNTGBSIBMLUOJT-UHFFFAOYSA-N 0.000 description 1
- OKDGEWZVSODHBT-UHFFFAOYSA-N ethyl 3-[[2-[[2-(benzylcarbamoylamino)-5-phenyl-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C(=C(S1)C=2C=CC=CC=2)N=C1NC(=O)NCC1=CC=CC=C1 OKDGEWZVSODHBT-UHFFFAOYSA-N 0.000 description 1
- APEVNZFNQCVULB-UHFFFAOYSA-N ethyl 3-[[2-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]propanoate Chemical compound CCOC(=O)CCNC(=O)CNC(=O)C1=CSC(NC(N)=N)=N1 APEVNZFNQCVULB-UHFFFAOYSA-N 0.000 description 1
- SWNXZTXDTUHCJM-UHFFFAOYSA-N ethyl 3-[[2-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]acetyl]amino]-3-phenylpropanoate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C=1SC(NC(N)=N)=NC=1C SWNXZTXDTUHCJM-UHFFFAOYSA-N 0.000 description 1
- SAKPWSGHWGPNHI-UHFFFAOYSA-N ethyl 3-[[2-[[2-(diaminomethylideneamino)-4-phenyl-1,3-thiazole-5-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound CCOC(=O)CC(NC(=O)CNC(=O)c1sc(NC(N)=N)nc1-c1ccccc1)c1ccccc1 SAKPWSGHWGPNHI-UHFFFAOYSA-N 0.000 description 1
- NMMWGMPCIYJGME-UHFFFAOYSA-N ethyl 3-[[2-[[2-(diaminomethylideneamino)-4-propyl-1,3-thiazole-5-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound CCCc1nc(NC(N)=N)sc1C(=O)NCC(=O)NC(CC(=O)OCC)c1ccccc1 NMMWGMPCIYJGME-UHFFFAOYSA-N 0.000 description 1
- NNEPQQGEAOSJIT-UHFFFAOYSA-N ethyl 3-[[2-[[2-(diaminomethylideneamino)-5-(3-nitrophenyl)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C=1N=C(NC(N)=N)SC=1C1=CC=CC([N+]([O-])=O)=C1 NNEPQQGEAOSJIT-UHFFFAOYSA-N 0.000 description 1
- IZLZBLVDEYVKPO-UHFFFAOYSA-N ethyl 3-[[2-[[2-(diaminomethylideneamino)-5-methyl-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C=1N=C(NC(N)=N)SC=1C IZLZBLVDEYVKPO-UHFFFAOYSA-N 0.000 description 1
- SPVHDETYCRKNHJ-UHFFFAOYSA-N ethyl 3-[[2-[[2-(diaminomethylideneamino)-5-phenyl-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C=1N=C(NC(N)=N)SC=1C1=CC=CC=C1 SPVHDETYCRKNHJ-UHFFFAOYSA-N 0.000 description 1
- NSSOJWNQGDYERA-UHFFFAOYSA-N ethyl 3-[[2-[[5-tert-butyl-2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C=1N=C(NC(N)=N)SC=1C(C)(C)C NSSOJWNQGDYERA-UHFFFAOYSA-N 0.000 description 1
- SKWVQYLJUGMLAV-UHFFFAOYSA-N ethyl 3-[[2-[cyclopropyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CN(C(=O)OC(C)(C)C)C1CC1 SKWVQYLJUGMLAV-UHFFFAOYSA-N 0.000 description 1
- IFMCYYAOWVOKPP-UHFFFAOYSA-N ethyl 3-[[3-[(2-methylpropan-2-yl)oxycarbonylamino]benzoyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C1=CC=CC(NC(=O)OC(C)(C)C)=C1 IFMCYYAOWVOKPP-UHFFFAOYSA-N 0.000 description 1
- VITMYLFYDVQYIE-UHFFFAOYSA-N ethyl 3-[[3-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]benzoyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C(C=1)=CC=CC=1NC(=O)C1=CSC(NC(N)=N)=N1 VITMYLFYDVQYIE-UHFFFAOYSA-N 0.000 description 1
- XPGDTTHMZKFRLK-UHFFFAOYSA-N ethyl 3-[[3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]-4-methoxybenzoyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C(C=1)=CC=C(OC)C=1NC(=O)C=1SC(NC(N)=N)=NC=1C XPGDTTHMZKFRLK-UHFFFAOYSA-N 0.000 description 1
- PNYRHDQKDJXHKL-UHFFFAOYSA-N ethyl 3-[[3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]benzoyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C(C=1)=CC=CC=1NC(=O)C=1SC(NC(N)=N)=NC=1C PNYRHDQKDJXHKL-UHFFFAOYSA-N 0.000 description 1
- IHSQTCXMSRDUGV-UHFFFAOYSA-N ethyl 3-[[4-[2-(diaminomethylideneamino)-4-methyl-1,3-thiazol-5-yl]benzoyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C(C=C1)=CC=C1C=1SC(NC(N)=N)=NC=1C IHSQTCXMSRDUGV-UHFFFAOYSA-N 0.000 description 1
- ZHWSPOBJRJAOBV-UHFFFAOYSA-N ethyl 3-[[5-amino-2-(2-methoxyethoxy)benzoyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C1=CC(N)=CC=C1OCCOC ZHWSPOBJRJAOBV-UHFFFAOYSA-N 0.000 description 1
- NUWRDXMXYDWUAN-UHFFFAOYSA-N ethyl 3-amino-3-phenylpropanoate Chemical compound CCOC(=O)CC(N)C1=CC=CC=C1 NUWRDXMXYDWUAN-UHFFFAOYSA-N 0.000 description 1
- GGANVLPLTUQZIF-UHFFFAOYSA-N ethyl 3-amino-3-pyridin-3-ylpropanoate;dihydrochloride Chemical compound Cl.Cl.CCOC(=O)CC(N)C1=CC=CN=C1 GGANVLPLTUQZIF-UHFFFAOYSA-N 0.000 description 1
- RJCGNNHKSNIUAT-UHFFFAOYSA-N ethyl 3-aminopropanoate;hydron;chloride Chemical compound Cl.CCOC(=O)CCN RJCGNNHKSNIUAT-UHFFFAOYSA-N 0.000 description 1
- OTKSIQOLKQEHMS-UHFFFAOYSA-N ethyl 3-phenyl-3-[3-(phenylmethoxycarbonylamino)propanoylamino]propanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CCNC(=O)OCC1=CC=CC=C1 OTKSIQOLKQEHMS-UHFFFAOYSA-N 0.000 description 1
- NXCIRGCOCWVPNI-UHFFFAOYSA-N ethyl 3-phenyl-3-[[2-[[2-(phenylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]propanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)CNC(=O)C(N=1)=CSC=1NC(=O)NC1=CC=CC=C1 NXCIRGCOCWVPNI-UHFFFAOYSA-N 0.000 description 1
- VZNBHLPEGALHOD-UHFFFAOYSA-N ethyl 4-[2-(benzylcarbamoylamino)-1,3-thiazol-4-yl]butanoate Chemical compound CCOC(=O)CCCC1=CSC(NC(=O)NCC=2C=CC=CC=2)=N1 VZNBHLPEGALHOD-UHFFFAOYSA-N 0.000 description 1
- XDYWTJHSXMXHPM-UHFFFAOYSA-N ethyl 4-amino-2-(4-chlorophenyl)-3-methylbutanoate Chemical compound CCOC(=O)C(C(C)CN)c1ccc(Cl)cc1 XDYWTJHSXMXHPM-UHFFFAOYSA-N 0.000 description 1
- OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 description 1
- QDWQJOXKKDTKDF-UHFFFAOYSA-N ethyl 4-methyl-2-(1,4,5,6-tetrahydropyrimidin-2-ylamino)-1,3-thiazole-5-carboxylate;hydrochloride Chemical compound Cl.CC1=C(C(=O)OCC)SC(N=C2NCCCN2)=N1 QDWQJOXKKDTKDF-UHFFFAOYSA-N 0.000 description 1
- SWFBUDHMLDCJAH-UHFFFAOYSA-N ethyl 5-oxo-6-[[2-(pyridin-2-ylmethylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]hexanoate Chemical compound CCOC(=O)CCCC(=O)CNC(=O)C1=CSC(NC(=O)NCC=2N=CC=CC=2)=N1 SWFBUDHMLDCJAH-UHFFFAOYSA-N 0.000 description 1
- LMVTWOKKNPZCBN-UHFFFAOYSA-N ethyl 6-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylhex-3-enoate Chemical compound CC(C)(C)OC(=O)NCCC=C(CC(=O)OCC)C1=CC=CC=C1 LMVTWOKKNPZCBN-UHFFFAOYSA-N 0.000 description 1
- KTOHWXGEDHQJKZ-UHFFFAOYSA-N ethyl 6-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]-3-phenylhexanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)CCCNC(=O)C(N=1)=CSC=1NC(=O)NCC1=CC=CC=C1 KTOHWXGEDHQJKZ-UHFFFAOYSA-N 0.000 description 1
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- DAEHOKOYMMZBPD-LBPRGKRZSA-N tert-butyl (3s)-3-amino-4-(3-methoxyanilino)-4-oxobutanoate Chemical compound COC1=CC=CC(NC(=O)[C@@H](N)CC(=O)OC(C)(C)C)=C1 DAEHOKOYMMZBPD-LBPRGKRZSA-N 0.000 description 1
- MTPOAFNEDYBPKG-IBGZPJMESA-N tert-butyl (3s)-4-(3-methoxyanilino)-4-oxo-3-(phenylmethoxycarbonylamino)butanoate Chemical compound COC1=CC=CC(NC(=O)[C@H](CC(=O)OC(C)(C)C)NC(=O)OCC=2C=CC=CC=2)=C1 MTPOAFNEDYBPKG-IBGZPJMESA-N 0.000 description 1
- SLGORGXSUYEVKH-NRFANRHFSA-N tert-butyl (3s)-4-(benzylamino)-3-[[2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-4-oxobutanoate Chemical compound N([C@@H](CC(=O)OC(C)(C)C)C(=O)NCC=1C=CC=CC=1)C(=O)CNC(=O)C(N=1)=CSC=1NC(=O)NCC1=CC=CC=C1 SLGORGXSUYEVKH-NRFANRHFSA-N 0.000 description 1
- DWEWVZASLUCTNR-IBGZPJMESA-N tert-butyl (3s)-4-(benzylamino)-4-oxo-3-(phenylmethoxycarbonylamino)butanoate Chemical compound N([C@@H](CC(=O)OC(C)(C)C)C(=O)NCC=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 DWEWVZASLUCTNR-IBGZPJMESA-N 0.000 description 1
- WZYPEPNPWZXPLB-IBGZPJMESA-N tert-butyl (3s)-4-anilino-3-[[3-[[2-(diaminomethylideneamino)-4-methyl-1,3-thiazole-5-carbonyl]amino]benzoyl]amino]-4-oxobutanoate Chemical compound N1=C(N=C(N)N)SC(C(=O)NC=2C=C(C=CC=2)C(=O)N[C@@H](CC(=O)OC(C)(C)C)C(=O)NC=2C=CC=CC=2)=C1C WZYPEPNPWZXPLB-IBGZPJMESA-N 0.000 description 1
- QMXMYHJQUJJLGE-KRWDZBQOSA-N tert-butyl (3s)-4-oxo-3-(phenylmethoxycarbonylamino)-4-piperidin-1-ylbutanoate Chemical compound N([C@@H](CC(=O)OC(C)(C)C)C(=O)N1CCCCC1)C(=O)OCC1=CC=CC=C1 QMXMYHJQUJJLGE-KRWDZBQOSA-N 0.000 description 1
- WDVYKTVVJLHCDR-IBGZPJMESA-N tert-butyl (3s)-4-oxo-4-(pyridin-2-ylmethylamino)-3-[[2-[[2-(pyridin-2-ylmethylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]butanoate Chemical compound N([C@@H](CC(=O)OC(C)(C)C)C(=O)NCC=1N=CC=CC=1)C(=O)CNC(=O)C(N=1)=CSC=1NC(=O)NCC1=CC=CC=N1 WDVYKTVVJLHCDR-IBGZPJMESA-N 0.000 description 1
- UDWHKSLUEHOYGJ-QHCPKHFHSA-N tert-butyl 2-[[(2s)-2-[[2-[[2-(benzylcarbamoylamino)-1,3-thiazole-4-carbonyl]amino]acetyl]amino]-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoyl]amino]benzoate Chemical compound N([C@@H](CC(=O)OC(C)(C)C)C(=O)NC=1C(=CC=CC=1)C(=O)OC(C)(C)C)C(=O)CNC(=O)C(N=1)=CSC=1NC(=O)NCC1=CC=CC=C1 UDWHKSLUEHOYGJ-QHCPKHFHSA-N 0.000 description 1
- AHBACTGRAGQAQB-ZDUSSCGKSA-N tert-butyl 2-[[(2s)-2-amino-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoyl]amino]benzoate Chemical compound CC(C)(C)OC(=O)C[C@H](N)C(=O)NC1=CC=CC=C1C(=O)OC(C)(C)C AHBACTGRAGQAQB-ZDUSSCGKSA-N 0.000 description 1
- JGZPMDHWKXZPLW-NRFANRHFSA-N tert-butyl 2-[[(2s)-4-[(2-methylpropan-2-yl)oxy]-4-oxo-2-(phenylmethoxycarbonylamino)butanoyl]amino]benzoate Chemical compound N([C@@H](CC(=O)OC(C)(C)C)C(=O)NC=1C(=CC=CC=1)C(=O)OC(C)(C)C)C(=O)OCC1=CC=CC=C1 JGZPMDHWKXZPLW-NRFANRHFSA-N 0.000 description 1
- HXHTZQHLBJRICM-UHFFFAOYSA-N tert-butyl 3-(benzylcarbamoyl)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate Chemical compound CC(C)(C)OC(=O)NCCCC(CC(=O)OC(C)(C)C)C(=O)NCC1=CC=CC=C1 HXHTZQHLBJRICM-UHFFFAOYSA-N 0.000 description 1
- SOUZTBGOBDIPIR-UHFFFAOYSA-N tert-butyl 3-[[3-[[2-(diaminomethylideneamino)-1,3-thiazole-4-carbonyl]amino]benzoyl]amino]propanoate Chemical compound CC(C)(C)OC(=O)CCNC(=O)C1=CC=CC(NC(=O)C=2N=C(NC(N)=N)SC=2)=C1 SOUZTBGOBDIPIR-UHFFFAOYSA-N 0.000 description 1
- DOMTZTVJNZKUNX-UHFFFAOYSA-N tert-butyl 3-aminopropanoate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)CCN DOMTZTVJNZKUNX-UHFFFAOYSA-N 0.000 description 1
- PRZGKHSPJLAXSZ-UHFFFAOYSA-N tert-butyl n-(2-aminoethanethioyl)carbamate Chemical compound CC(C)(C)OC(=O)NC(=S)CN PRZGKHSPJLAXSZ-UHFFFAOYSA-N 0.000 description 1
- BAEFUAYRWLKGRC-UHFFFAOYSA-N tert-butyl n-(4-oxo-4-phenylbutyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCC(=O)C1=CC=CC=C1 BAEFUAYRWLKGRC-UHFFFAOYSA-N 0.000 description 1
- DJDVCMJMJKSDTB-UHFFFAOYSA-N tert-butyl n-(5-oxo-5-phenylpentyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCCC(=O)C1=CC=CC=C1 DJDVCMJMJKSDTB-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- ZMCBYSBVJIMENC-UHFFFAOYSA-N tricaine Chemical compound CCOC(=O)C1=CC=CC(N)=C1 ZMCBYSBVJIMENC-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- GSQBIOQCECCMOQ-UHFFFAOYSA-N β-alanine ethyl ester Chemical compound CCOC(=O)CCN GSQBIOQCECCMOQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Oncology (AREA)
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- Rheumatology (AREA)
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- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| EP98100006.0 | 1998-01-02 | ||
| EP98100006 | 1998-01-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2000053664A JP2000053664A (ja) | 2000-02-22 |
| JP3113237B2 true JP3113237B2 (ja) | 2000-11-27 |
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| KR (1) | KR100312901B1 (pt) |
| CN (1) | CN1080720C (pt) |
| AR (1) | AR014949A1 (pt) |
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| ES (1) | ES2193471T3 (pt) |
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| ID (1) | ID21936A (pt) |
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| MA (1) | MA26591A1 (pt) |
| NO (1) | NO312067B1 (pt) |
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| PT (1) | PT928790E (pt) |
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| US6911462B2 (en) * | 1998-05-22 | 2005-06-28 | Avanir Pharmaceuticals | Benzimidazole compounds for regulating IgE |
| US6919366B2 (en) * | 1998-05-22 | 2005-07-19 | Avanir Pharmaceuticals | Benzimidazole derivatives as modulators of IgE |
| GB9826174D0 (en) * | 1998-11-30 | 1999-01-20 | Celltech Therapeutics Ltd | Chemical compounds |
| AU5826100A (en) | 1999-07-13 | 2001-01-30 | F. Hoffmann-La Roche Ag | Benzazepinones and quinazolines |
| US6759425B2 (en) * | 1999-10-21 | 2004-07-06 | Avanir Pharmaceuticals | Benzimidazole compounds for modulating IgE and inhibiting cellular proliferation |
| KR100766158B1 (ko) * | 2000-01-19 | 2007-10-10 | 알테온 인크. | 티아졸, 이미다졸 및 옥사졸 화합물, 및 단백질 노화와관련된 장애의 치료 |
| RU2003127367A (ru) * | 2001-03-12 | 2005-03-20 | Аванир Фармасьютиклз (Us) | Бензимидазоловые соединения для модулирования ige и ингибирования клеточной пролиферации |
| PE20030968A1 (es) * | 2002-02-28 | 2004-01-12 | Novartis Ag | Derivados de 5-feniltiazol como inhibidores de cinasas |
| TW200304820A (en) * | 2002-03-25 | 2003-10-16 | Avanir Pharmaceuticals | Use of benzimidazole analogs in the treatment of cell proliferation |
| TWI276631B (en) * | 2002-09-12 | 2007-03-21 | Avanir Pharmaceuticals | Phenyl-aza-benzimidazole compounds for modulating IgE and inhibiting cellular proliferation |
| AU2003270426A1 (en) | 2002-09-12 | 2004-04-30 | Avanir Pharmaceuticals | PHENYL-INDOLE COMPOUNDS FOR MODULATING IgE AND INHIBITING CELLULAR PROLIFERATION |
| AU2004263190A1 (en) * | 2003-08-08 | 2005-02-17 | Avanir Pharmaceuticals | Selective pharmacologic inhibition of protein trafficking and related methods of treating human diseases |
| US7652146B2 (en) * | 2004-02-06 | 2010-01-26 | Bristol-Myers Squibb Company | Process for preparing 2-aminothiazole-5-carboxamides useful as kinase inhibitors |
| EP1797084A1 (en) * | 2004-09-20 | 2007-06-20 | 4Sc Ag | NOVEL HETEROCYCLIC NF-kB INHIBITORS |
| WO2008011191A1 (en) * | 2006-07-21 | 2008-01-24 | Replidyne, Inc. | Antibacterial heterocyclic ureas |
| WO2009015193A1 (en) * | 2007-07-23 | 2009-01-29 | Replidyne, Inc. | Antibacterial sulfone and sulfoxide substituted heterocyclic urea compounds |
| WO2009015208A1 (en) | 2007-07-23 | 2009-01-29 | Replidyne, Inc. | Antibacterial amide and sulfonamide substituted heterocyclic urea compounds |
| TWI504598B (zh) * | 2009-03-20 | 2015-10-21 | Onyx Therapeutics Inc | 結晶性三肽環氧酮蛋白酶抑制劑 |
| CN102936257B (zh) * | 2012-08-30 | 2016-03-30 | 齐鲁工业大学 | 一类含银的噻唑西弗碱配合物的结构、制备和用途 |
| WO2019002074A1 (en) | 2017-06-29 | 2019-01-03 | Bayer Aktiengesellschaft | THIAZOLE COMPOUNDS USEFUL AS INHIBITORS OF PRMT5 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2009155B (en) * | 1977-11-07 | 1982-07-21 | Leo Pharm Prod Ltd | Chemical compounds |
| FR2581063B1 (fr) | 1985-04-30 | 1987-07-17 | Chauvin Blache Lab | Amino-2 thiazoles n-substitues, leur procede de preparation et leur application en therapeutique |
| JPS62123180A (ja) * | 1985-11-21 | 1987-06-04 | Otsuka Pharmaceut Factory Inc | ｐ−アミノフエノ−ル誘導体 |
| US5000775A (en) * | 1985-12-31 | 1991-03-19 | Monsanto Company | 2-amino-4,5-disubstituted-oxazole/thiazole compounds as herbicide antidotes |
| JPS6348873A (ja) * | 1986-08-19 | 1988-03-01 | Toshiba Corp | ガスレ−ザ発振装置 |
| CA2037153A1 (en) * | 1990-03-09 | 1991-09-10 | Leo Alig | Acetic acid derivatives |
| US5273982A (en) * | 1990-03-09 | 1993-12-28 | Hoffmann-La Roche Inc. | Acetic acid derivatives |
| FI922867A (fi) * | 1991-06-21 | 1992-12-22 | Tanabe Seiyaku Co | Dikarbonsyraderivat och foerfarande foer framstaellning av dem |
| US5294713A (en) * | 1991-08-23 | 1994-03-15 | Takeda Chemical Industries, Ltd. | 2-piperazinone compounds and their use |
| GB9125970D0 (en) * | 1991-12-06 | 1992-02-05 | Fujisawa Pharmaceutical Co | New compounds |
| US5514643A (en) * | 1993-08-16 | 1996-05-07 | Lucky Ltd. | 2-aminothiazolecarboxamide derivatives, processes for preparing the same and use thereof for controlling phytopathogenic organisms |
| US6306840B1 (en) * | 1995-01-23 | 2001-10-23 | Biogen, Inc. | Cell adhesion inhibitors |
| JPH08337579A (ja) * | 1995-06-14 | 1996-12-24 | Fujisawa Pharmaceut Co Ltd | グアニジノチアゾ−ルおよびその抗潰瘍剤、ｈ２−受容体拮抗剤および抗菌剤としての用途 |
| JPH09295974A (ja) * | 1995-09-11 | 1997-11-18 | Nippon Nohyaku Co Ltd | アゾール誘導体、その用途及びその製造方法並びにその使用方法 |
| NZ299242A (en) * | 1995-09-11 | 1997-12-19 | Nihon Nohyaku Co Ltd | N-phenyl-n'-(phenyl substituted imidazol-5-yl, -oxazol-4-yl, and -thiazol-4-yl)urea derivatives |
| WO1997024343A1 (en) * | 1995-12-29 | 1997-07-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Phenyl thiazole derivatives with anti herpes virus properties |
| MA26487A1 (fr) * | 1997-04-29 | 2004-12-20 | Smithkline Beecham Corp | Heterocyclecetohydrazides inhibiteurs de proteases, procede pour leur preparation et compositions pharmaceutiques les contenant . |
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1998
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- 1998-12-30 HU HU9803040A patent/HUP9803040A3/hu unknown
- 1998-12-30 AU AU96144/98A patent/AU720618B2/en not_active Ceased
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2000
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2001
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